Director Of Alumni Engagement

Shady Side Academy•Pittsburgh, PA

3d•Onsite

About The Position

Shady Side Academy seeks a Director of Alumni Engagement to build meaningful, lasting relationships with alumni across generations and around the country. Reporting to the Chief Philanthropy Officer and working within the Alumni & Development Office, the Director leads a comprehensive strategy spanning programs, events, volunteer opportunities, and connections. The strategy is intended to strengthen alumni affinity, expand participation, and create opportunities for alumni to contribute their time, expertise, networks, and philanthropic support. The Director will build on existing traditions and develop new programs and approaches to shape the future of alumni engagement at the Academy. This highly relational and visible role calls for a self-directed, creative professional who can advance strategic direction, identify creative solutions, and move ideas from concept through execution. The role is full-time, 12-month, and in-person, with periodic travel and some evening and weekend responsibilities.

Requirements

Bachelor’s degree.
A minimum of three to five years of relevant experience in alumni relations, advancement, fundraising, volunteer engagement, community building, event programming, or a related field.
Exceptional interpersonal skills and demonstrated ability to build authentic relationships with people across generations, backgrounds, and experiences.
Strong written and verbal communication skills, with the judgment and presence to represent Shady Side Academy with clarity, warmth, and credibility.
Ability to manage complex programs, events, timelines, and competing priorities with strong organization and follow-through.
Experience recruiting, motivating, and supporting volunteers, advisory groups, boards, or committees.
Collaborative working style and ability to build productive partnerships across teams while taking ownership of projects and priorities.
Comfort using data to understand engagement, evaluate programs, and inform decisions.
Proficiency with Google Workspace and Microsoft Office, and ability to learn CRM, donor database, event, and communications platforms.
Demonstrated ability to use project management software to organize work, coordinate tasks and responsibilities across colleagues and stakeholders, and manage timelines and deliverables effectively.
Commitment to Shady Side Academy’s mission, guiding principles, and community norms.

Nice To Haves

Experience within independent schools, higher education, or mission-driven organizations is particularly relevant.
Experience with Raiser’s Edge, Veracross, or similar systems is beneficial.
Strategic and creative thinking, including developing new approaches to engagement and translating ideas into well-executed programs and experiences.
Growth-oriented mindset.

Responsibilities

Design a data-informed portfolio of alumni experiences, including regional gatherings, professional and networking opportunities, affinity programming, virtual engagement, and signature Academy events.
Lead the strategy, planning, and execution of Homecoming & Reunion Weekend to welcome alumni across generations and strengthen their connection to the Academy.
Develop programming responsive to different stages of the alumni experience, from recent graduates to milestone reunion classes and longtime alumni.
Create opportunities for alumni to engage in the life of the Academy through mentorship, career connections, student experiences, institutional initiatives, and other meaningful forms of participation.
Use alumni data, participation trends, and feedback to evaluate programming and identify opportunities to deepen engagement.
Serve as a visible and responsive ambassador for Shady Side Academy at alumni events and gatherings locally and regionally.
Recruit, cultivate, and support alumni volunteers who extend the Academy’s reach through events, peer engagement, reunion leadership, and philanthropy.
Serve as staff liaison to the Alumni Council and partner with the Chief Philanthropy Officer to support the Board of Visitors.
Develop strong relationships with reunion leaders, regional alumni volunteers, affinity groups, and other alumni ambassadors.
Partner with the Director of Annual Giving to develop reunion engagement and giving strategies, establish participation and fundraising goals, and support effective peer outreach.
Integrate opportunities for philanthropy into alumni programs while maintaining a relationship-centered approach to engagement.
Identify alumni interests, relationships, and engagement signals that may create opportunities for deeper involvement with the Academy, and share relevant insights with Annual Giving and Major Gifts colleagues.
Partner with the Marketing & Communications Office to identify alumni stories that demonstrate the impact of the Shady Side experience beyond campus.
Collaborate across Alumni & Development, Marketing & Communications, Enrollment Management, Athletics, academic leadership, and other Academy areas to incorporate alumni stories into institutional communications, programs, and engagement opportunities.
Ensure alumni programs and communications reflect Shady Side Academy’s mission, guiding principles, brand, and institutional priorities.